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Evolution Der Detoxifizierung Und Bioaktivierung Von Benzoxazinoid-Sekundärmetaboliten Regina Dick

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Evolution Der Detoxifizierung Und Bioaktivierung Von Benzoxazinoid-Sekundärmetaboliten Regina Dick TECHNISCHE UNIVERSITÄTMÜNCHEN Lehrstuhl für Genetik Evolutionder Detoxifizierung und Bioaktivierungvon BenzoxazinoidSekundärmetaboliten ReginaDick Vollständiger Abdruck der von der Fakultät Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt der Technischen Universität München zur Erlangung des akademischen Grades eines Doktors der Naturwissenschaften genehmigten Dissertation. Vorsitzender: Univ.-Prof. Dr. K. Schneitz Prüfer der Dissertation: 1. Univ.-Prof. Dr. A. Gierl 2. Univ.-Prof. Dr. E. Grill 3. Univ.-Prof. Dr. W. Schwab Die Dissertation wurde am 07.07.2010 bei der Technischen UniversitätMünchen eingereichtund durch die Fakultät Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt am 09.09.2010 angenommen. Inhaltsverzeichnis I Inhaltsverzeichnis Inhaltsverzeichnis ................................................................................................................... I Abkürzungsverzeichnis .......................................................................................................... V 1 Einleitung ...................................................................................................................... 1 1.1 Sekundäre Pflanzeninhaltsstoffe .............................................................................. 1 1.1.1 Funktion von sekundären Pflanzeninhaltsstoffen .............................................. 1 1.1.2 Sekundäre Pflanzeninhaltsstoffe als Abwehrsubstanzen .................................. 1 1.2 Detoxifizierung und Bioaktivierung von Phytoantizipinen: UGTs und β-Glucosidasen des Sekundärstoffwechsels ............................................................ 4 1.2.1 UDP-abhängige Glycosyltransferasen (UGTs) der Familie 1 ............................ 5 1.2.2 β-Glucosidasen der Familie 1 (GH1) ................................................................. 8 1.3 Benzoxazinoid-Glucoside als Modellsystem der Phytoantizipin Biosynthese ......... 12 1.3.1 Biosynthese und Bioaktivierung in Gräsern .................................................... 14 1.3.2 Biosynthese in den dikotylen Pflanzen C. orientalis und L. galeobdolon ......... 15 1.3.3 Untersuchungen zur Evolution der Benzoxazinoid-Biosynthese in monokotylen und dikotylen Pflanzen ............................................................... 16 1.4 Ziel der Arbeit ........................................................................................................ 17 2 Material und Methoden ............................................................................................... 18 2.1 Materialien ............................................................................................................. 18 2.1.1 Chemikalien und Reagenzien ......................................................................... 18 2.1.2 Phagenbanken ............................................................................................... 18 2.1.3 Plasmide ......................................................................................................... 19 2.1.4 Bakterienstämme ............................................................................................ 19 2.1.5 Oligonukleotide ............................................................................................... 19 2.1.6 Pflanzenmaterial und Anzucht ........................................................................ 23 2.2 Molekularbiologische Methoden ............................................................................. 24 2.2.1 DNA-Isolierung ............................................................................................... 24 2.2.2 RNA-Isolierung und cDNA-Synthese .............................................................. 24 2.2.3 Analyse der RNA durch Formaldehyd-Agarosegel-Elektrophorese ................. 24 Inhaltsverzeichnis II 2.2.4 Allgemeine DNA-Klonierungstechniken .......................................................... 24 2.2.5 Design und Klonierung von amiRNA-Konstrukten ........................................... 25 2.2.6 PCR-Verfahren ............................................................................................... 25 2.2.7 Verfahren zur Isolierung von 5´- und 3´-cDNA-Enden ..................................... 26 2.2.8 Isolierung von UDPG:Glycosyltransferase-Kandidatenteilsequenzen aus L. galeobdolon ................................................................................................ 27 2.2.9 DNA-Sequenzierung ....................................................................................... 27 2.2.10 Sequenzierung des C. orientalis Transkriptoms .............................................. 27 2.2.11 Screening von cDNA-Bibliotheken durch Phagenhybridisierung ..................... 28 2.3 Proteinbiochemische Methoden ............................................................................. 29 2.3.1 Reinigung von Co BX8 und Lg BX8 aus C. orientalis bzw. L. galeobdolon ....... 29 2.3.2 Proteinfällung.................................................................................................. 31 2.3.3 SDS-Polyacrylamid-Elektrophorese (SDS-PAGE) .......................................... 31 2.3.4 Proteinkonzentrationsbestimmung nach Bradford ........................................... 31 2.3.5 Heterologe Proteinexpression in E. coli und Reinigung über Nickel- Affinitätschromatographie ............................................................................... 31 2.4 Isolierung von Naturstoffen .................................................................................... 32 2.4.1 Isolierung von DIBOA aus L. galeobdolon bzw. DIMBOA aus Z. mays ........... 32 2.4.2 Isolierung von GDIBOA aus L. galeobdolon .................................................... 33 2.4.3 Isolierung von GDIMBOA aus Z. mays ........................................................... 33 2.5 Analyse von Naturstoffen ....................................................................................... 33 2.5.1 Hoch-Durchsatz-Flüssigkeitschromatographie (HPLC) ................................... 33 2.6 Enzymtests ............................................................................................................ 36 2.6.1 Tests auf Glucosyltransferase-Aktivität ........................................................... 36 2.6.2 Tests auf β-Glucosidase-Aktivität ................................................................... 37 2.7 Elektroporation von Agrobakterien ......................................................................... 39 2.8 Transiente Proteinexpression in N. benthamiana ................................................... 39 2.8.1 Agroinfiltration ................................................................................................. 40 2.8.2 Proteinextraktion aus N. benthamiana ............................................................ 40 2.9 Erzeugung und Analyse von transgenen A. thaliana -Pflanzen ............................... 41 Inhaltsverzeichnis III 2.9.1 Elektroporation von Agrobakterien und Transformation von A. thaliana mit A. tumefaciens ................................................................................................ 41 2.9.2 Analyse der transgenen A. thaliana-Pflanzen ................................................. 41 2.10 Expression von amiRNA-Konstrukten in Z. mays ................................................... 41 2.10.1 Analyse transgener Z. mays -Pflanzen ............................................................ 42 3 Ergebnisse .................................................................................................................. 43 3.1 Isolierung der UDPG:DIBOA Glucosyltransferasen und Flavonoid Glucosyl- transferasen aus C. orientalis und L. galeobdolon ................................................. 43 3.1.1 Reinigung von Co BX8 und p Lg BX8 ................................................................ 44 3.1.2 Identifizierung der CoBx8-, p LgBx8-, CoGT- und Lg GT- Gensequenzen ........ 47 3.2 Charakterisierung der heterolog exprimierten Proteine Co BX8, Co GT und Lg GT .. 53 3.2.1 Expression und Reinigung von Co BX8, p Lg BX8, Co GT und Lg GT ................. 53 3.2.2 Substratspezifität von Co GT und Lg GT .......................................................... 53 3.2.3 Kinetische Daten von Co BX8 .......................................................................... 54 3.2.4 Substratspezifität von Co BX8 ......................................................................... 56 3.2.5 Vergleich der Co BX8 und p Lg BX8 Proteinsequenzen mit anderen Glycosyltransferasen ...................................................................................... 57 3.2.6 Genexpressionsanalyse von CoBx8 ............................................................... 58 3.3 Funktion von Co BX8 in planta ............................................................................... 59 3.3.1 Enzymatische Aktivität von Co BX8 in Arabidopsis -Pflanzen ........................... 59 3.3.2 Resistenztests der transgenen Arabidopsis -Pflanzen ..................................... 60 3.4 Isolierung der Benzoxazinoid-Glucosid β-Glucosidase aus C. orientalis ................ 61 3.4.1 Identifizierung von Benzoxazinoid-Glucoisd β-Glucosidase Kandidaten Gensequenzen ............................................................................................... 61 3.4.2 Transgene Expression der Benzoxazinoid-Glucosid β-Glucosidase-Kandidaten in N. benthamiana .........................................................................................
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